39904-00-2

Basic information

• Product Name: (1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol
• Synonyms: (1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol
• CAS NO: 39904-00-2
• Molecular Weight: 172.268
• Mol File: 39904-00-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol(39904-00-2)
• EPA Substance Registry System: (1R,2S,4S)-4-isopropyl-1-methylcyclohexane-1,2-diol(39904-00-2)

Safety Data

• Hazardous Substances Data: 39904-00-2(Hazardous Substances Data)

Upstream product

• 1946-00-5 (1RS,2SR,4RS)-p-menth-8-ene-1,2-diol 
• 61585-35-1 p-menth-1-ene 
• 39903-74-7 (1S,2S,3R,5R)-2,3-epoxy-5-isopropenyl-2-methylcyclohex-2-enol 
• 5989-54-8 (-)-(S)-limonene 
• 499-94-5 (S)-carvomenthene 
• 39903-99-6 (1R,2S,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol 
• 138-86-3 limonene. 
• 1195-92-2 Limonene oxide 

Downstream Products

• 499-70-7 methyl-2 isopropyl-5 cyclohexanone 
• 160168-89-8 (5S)-2-methyl-5-(methylethyl)cyclohexan-1-one 
• 57457-93-9 (-)1-hydroxy-carvomenthone 
• 2102-60-5 (+/-)-3,5-dinitro-benzoic acid-(trans-p-menth-6-en-2-yl ester) 

Relevant articles and documents

Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers

(S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (±)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide.